The secret to telling a joke and getting on HBO, according to ‘Crashing’ stars Pete Holmes and Jamie Lee

CHICAGO – Telling funny jokes is hard. Creating a hit HBO series is harder. How do you do it?

Business Insider caught up with Pete Holmes and Jamie Lee on Thursday while they were in Chicago to promote season two of “Crashing,” the HBO series executive-produced by Judd Apatow about making it in standup – or, in Holmes’ words, “the worst parts of standup.”

Daniel McMahon: What’s the secret to telling a good joke?

Pete Holmes: Meaning it. [Laughs] I asked Glen Hansard, from the movie “Once” and the band The Frames, because he really belts out his songs, and I was, like, “How do you not lose your voice?” And he said, “Meaning it.” And I think there’s something about the great comedians I’ve seen – and just great joke tellers – that they are really in the joke.

They’re not thinking about the end, they’re not thinking about the middle or the beginning. They’re just kind of right there with you. And I think that’s what people connect to and makes them feel safe to laugh.

Jamie Lee: Right before I go onstage, I try to get really psyched about myself. Like, I allow myself to have a really almost narcissistic wave take over, where not only is what I have to say really important, but I’m psyched to say it. I think it helps. It’s a little “fake it till you make it.” But when you go onstage it’s, like, “Boy, are you guys in for a treat.”

Holmes: Can I add to that? First of all, it’s in Judy Carter’s book, which we both read. It’s not her exact point, but she said you should get onstage or tell a joke or talk to a stranger as if you’re seeing a friend you’ve been waiting to see all day. And I think that’s wonderful.

When I used to work the road, I remember I used to ask myself in the mirror, literally, like in a movie, back when I was not very good at all, I’d say, “What’s it like being the greatest comedian in the world?” Like in an interview, like this, I’d imagine you, Daniel, asking me, “What’s it like being the greatest comedian in the world?” And it would get me into that necessary confidence. Not cockiness, but certainty. And people love certainty. They love following certain people. A joke is a journey, and you’re taking them on it.

Lee: When you’re onstage you’re a Sherpa, and if you make them feel like you’re someone they can trust, whatever you’re saying almost melts away. It’s an attitude.

Holmes: That’s why you can laugh at a comedian who you don’t agree with, or you think they’re offensive. In that moment you can be swept away.

McMahon: So now you’ve made it on HBO –

Holmes: And HBO GO!

Lee: I’m only excited to be on HBO GO.

McMahon: What advice would you give to comedians or artists trying to make it?

Holmes: You have to do something that kind of doesn’t make sense. One is, have goals, like being on HBO or being in a movie or having a book or being in a museum, whatever it might be. And also forget those goals and focus on the day-to-day, that moment. What are you doing with this crowd, with this project, and don’t get too caught up with “Have I made it?” “Do I have enough respect or money or prestige?” But at the same time, know where you’re aiming, but once you’re up in the sky, just know that you’re heading in the right direction. That’s all that matters.

Lee: When you’re starting out, you should just focus on getting good and getting to a place where you feel confident and self-assured, because that does take a while to feel that genuinely. But at a certain point you should just start saying what you want out loud, because for me, I was always kind of embarrassed to admit, for example, that I always wanted to act. I was, like, “No! Ew! Acting!” Like, “I don’t want to go down that path. That sounds like a nightmare.” But the second I started allowing myself to admit the things that I wanted, I feel like they did start to happen more. I think people should say the things they want and try to not feel shame about them.

Holmes: Green-light your desires and your goals. Keep them to yourself. And just sweep the floor.

The new season of “Crashing” premieres Sunday, January 14, on HBO.

Below you can watch the trailer for season two and see some photos from Thursday’s Chicago event hosted by the AV Club at Blu Dot:

The Chicago premiere of HBO’s second season of “Crashing” was hosted by The A.V. Club at the Blu Dot modern-furniture store.

A furniture story was the perfect setting for the “Crashing” premiere, a show that follows the struggling comedian Pete (Pete Holmes) as he tries to make it in New York City’s standup scene — and spends lots of nights crashing on friends’ couches.